Chestertown
Chestertown was chartered in 1706 as a town, on land that had been a 100 acre land grant owned by Simon Wilmer. During Colonial times it was a significant port, receiving foreign goods and exporting tobacco that was grown on the Eastern Shore. Ships sailed to and from Baltimore. By the Revolutionary War, its importance as a port had diminished, but some very interesting historic architecture remain.
Brick sidewalks and shade trees adorn the main streets of the historic district of Chestertown, with fine examples of Georgian, Federal and Victorian homes bringing a visitor back in time.
The Hynson-Ringgold House was built in 1743 and was said to have been a meeting place for officers associated with the port. Most notable is the Antler Staircase in the home which was said to have been designed by architect William Buckland. Another home worthy of mention is Widehall, which was built in 1769 in the Georgian style, by wealthy merchant Thomas Smythe, who is a notable Revolutionary War figure. Along Water Street, Colonial brick mansions built by wealthy merchants during the mid 18th century grace the waterfront. There are also many homes of the Victorian era, with their gingerbread trim and wraparound porches.
Chestertown is also home of Washington College, one of the oldest Liberal Arts colleges in the country, which was founded in 1782 with the help of George Washington, who served as a trustee, and was given an honorary degree from the college. Now, the college serves as the community's intellectual stimulation with many lectures and well-known speakers.
Visitors are drawn to Chestertown because of its beautiful historic charm, which has been thoughtfully preserved and maintained. Culture abounds in the little town, with art galleries and antique shops staying open late once a month, on First Fridays.
The Chestertown Tea Party is one of many festivals held throughout the year. The Tea Party commemorates the rebellion of the townspeople over the taxation of tea by the British during Colonial times, when cargoes of tea were dumped into the river. This event held Memorial Day weekend attracts thousands to the area and heralds the beginning of the summer vacation season.
For gourmet light fare be sure to stop at the Old Mill Bakery & Café or for formal fine dinning the Imperial Hotel awaits you. There are numerous other dining venues to choose from, all within walking distance. A short stroll along High Street will lead you in and out of many interesting shops and art galleries. No matter what you're looking for, you can find it in Chestertown.
